Issue 30, 2023

Lewis/Brønsted acid-mediated cyclization/amidation of 1,6-enynes with nitriles: access to 3-enamide substituted dihydrobenzofurans

Abstract

A novel Lewis- and Brønsted-acid mediated electrophilic addition cyclization/amidation reaction of 1,6-enynes with nitriles to synthesize 3-enamide-substituted dihydrobenzofurans has been developed. The transformation involves the addition of a Brønsted acid as the electrophilic reagent to enynes, followed by intramolecular cyclization to form cationic intermediates, and the termination of the reaction by a nitrile as a nucleophile. The main features of the reaction include high atom economy and chemoselectivity, as well as the construction of C–C/C–N bonds in one step.

Graphical abstract: Lewis/Brønsted acid-mediated cyclization/amidation of 1,6-enynes with nitriles: access to 3-enamide substituted dihydrobenzofurans

Supplementary files

Article information

Article type
Communication
Submitted
20 Feb 2023
Accepted
18 Mar 2023
First published
28 Mar 2023

Chem. Commun., 2023,59, 4523-4526

Lewis/Brønsted acid-mediated cyclization/amidation of 1,6-enynes with nitriles: access to 3-enamide substituted dihydrobenzofurans

Z. Chen, W. Huang, Y. Su, H. Jiang and W. Wu, Chem. Commun., 2023, 59, 4523 DOI: 10.1039/D3CC00787A

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